Water → Acetate 1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-methanol acetate

HRID 441610

反応式

HRID 441610 の反応式
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:9][CH:8]=[C:7]([CH2:10][CH2:11][OH:12])[C:5]=2[CH:6]=1.[C:13]([O:16][CH2:17][C:18]([CH3:20])=O)(=[O:15])[CH3:14].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1.C(OCC)(=O)C>[C:13]([O:16][CH2:17][C:18]1([CH3:20])[C:8]2[NH:9][C:4]3[C:5]([C:7]=2[CH2:10][CH2:11][O:12]1)=[CH:6][CH:1]=[CH:2][CH:3]=3)(=[O:15])[CH3:14].[C:13]([OH:16])(=[O:15])[CH3:14]

参加物

7

反応物 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 10685TryptopholHCID 11593Acetoxyacetone

生成物 1

HCID 70622673Acetate 1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-methanol acetate

試薬・触媒・溶媒 2

HCID 241Benzene溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of the starting material, tryptophol (32.2 g, 0.2 mole), acetonyl acetate (23.2 g, 0.2 mole) and 3.2 g of p-toluenesulfonic acid in 500 ml of benzene is refluxed for 11/2 hr. in the presence of a Dean-Stark water trap. The benzene solution is washed with 5% sodium bicarbonate, water, dried and evaporated to afford an oil. The oil is subjected to chromatography on a silica gel column using 10% ethyl acetate in benzene as eluent. The acetate 1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-methanol acetate is obtained as an oil, nmr(CDCl3) δ1.52 (S,3H), 2.08(S,3H), 4.35(2H).

後処理

  1. temperatureis refluxed for 11/2 hr
  2. washThe benzene solution is washed with 5% sodium bicarbonate, water
  3. customdried
  4. customevaporated
  5. customto afford an oil

出典と根拠

ORDレコード
ord-efa17d787a1c41568769d38659e0253a
出典データセット
uspto-grants-1977_08
特許番号
US04041169

関連ノート

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